Prenderol (Diethylpropanediol) is a simple alkyl diol which has sedative, anticonvulsant and muscle relaxant effects. It is closely related in structure to meprobamate and numerous other alkyl alcohols and diols with generally comparable activity.[1][2][3][4][5][6]
Synthesis
The hydroxymethylation 2-ethylbutyraldehyde [97-96-1] with aqueous formaldehyde and potassium hydroxide followed by Cannizzaro-type disproportionation afforded a 76% yield of product.[7]
The above method avoids the handling of lithium aluminium hydride, which would be necessary when starting from tetraethyl malonate [77-25-8] (the precursor needed to make Barbital).
Precursor
Prenderol is used as precursor for the following list of compounds:
- Metuchen [6009-77-4]
- Prenderol Dinitrate (PRDN):[8]
- Diethadione[9][10]
See also
- 1,4-Butanediol
- 1,6-Dioxecane-2,7-dione
- 1-Ethynylcyclohexanol
- 2-Methyl-2-propyl-1,3-propanediol
- 2-Methyl-2-butanol
- 2-Methyl-2-pentanol
- 3-Methyl-3-pentanol
- 3-Hydroxybutanal
- Ethchlorvynol
- Phenaglycodol
References
- ^ Berger FM (June 1949). "Anticonvulsant action of 2-substituted-1,3-propanediols". Proceedings of the Society for Experimental Biology and Medicine. 71 (2). New York, N.Y.: 270–271. doi:10.3181/00379727-71-17159. PMID 18134033. S2CID 32255832.
- ^ Funderburk WH, Unna KR (March 1953). "Site of action of 2, 2-diethyl-1,3-propanediol (prenderol) on the central nervous system". The Journal of Pharmacology and Experimental Therapeutics. 107 (3): 344–55. PMID 13035673.
- ^ Mailer AB (July 1954). "Effects of mephenesin and prenderol on intellectual functions of mental patients". Journal of Clinical Psychology. 10 (3): 283–5. doi:10.1002/1097-4679(195407)10:3<283::aid-jclp2270100322>3.0.co;2-a. PMID 13163224.
- ^ Blum B (May 1962). "Head shaking and nystagmus produced by 2,2-diethyl, 1,3-propanediol (prenderol) in the rat". Archives Internationales de Pharmacodynamie et de Therapie. 137: 128–36. PMID 13870189.
- ^ Reyes Q., Aaurelio; Mascetti V., G.; Martinez J., Rolando. Synthesis of polyhydroxylated alcohols. Revista Latinoamericana de Quimica 1984; 15 (1): 29-30. ISSN: 0370-5943.
- ^ Wang G, Lu Q (October 2013). "A nitrate ester of sedative alkyl alcohol improves muscle function and structure in a murine model of Duchenne muscular dystrophy". Molecular Pharmaceutics. 10 (10): 3862–70. doi:10.1021/mp400310r. PMID 23924275.
- ^ McKusick, B. (May 1948). "New Compounds. New Compounds as Insect Repellents". Journal of the American Chemical Society. 70 (5): 1982–1983. doi:10.1021/ja01185a602.
- ^ Petersen Aage, et al. U.S. patent 3,251,739 (1966 to APOTHEKERNES LAB).
- ^ Testa, Emilio; Fontanella, Luigi; Cristiani, Gianfranco; Gallo, Giangualberto (1959). "5,5-Disubstituted Dihydro-1,3-oxazine-2,4-diones. Research on Compounds Active on Central Nervous System. XII1a". The Journal of Organic Chemistry. 24 (12): 1928–1936. doi:10.1021/jo01094a026.
- ^ Testa Emilio, GB855244 (1960 to Lepetit, SpA).
Recent Comments